Heteroarylcyanine Dyes

Active Publication Date: 2014-01-02
PACIFIC BIOSCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides dyes and conjugates that improve the performance of dyes in optical assays by enhancing their hydrophilicity and reducing blinking, aggregation, and photobleaching. These dyes have been engineered to have useful emissions for DNA sequencing and provide greater sensitivity and accuracy compared to current dyes. The invention also includes a versatile linker arm that allows for the attachment of the label to a carrier molecule in a variety of positions on the cyanine nucleus. The compounds of the invention are particularly useful in single molecule or real-time DNA sequencing assays, where multiple fluorophores can be utilized and distinguished. The use of compounds of the invention in these assays enhances performance by at least about 10% over a similar assay using currently available fluorophores.

Problems solved by technology

Previous dyes used in such applications have less than ideal properties.
For example, certain dyes give suboptimal performance, because, as was discovered, the dyes are insufficiently hydrophilic, insufficiently bright, do not emit steadily (i.e., blink), undergo photobleaching upon prolonged irradiation, or they aggregate.
These deficiencies can cause misreads in DNA sequencing analyses, providing inaccurate results.

Method used

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  • Heteroarylcyanine Dyes
  • Heteroarylcyanine Dyes
  • Heteroarylcyanine Dyes

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of A and B

[0233]

[0234]To 0.255 g of 3,5-dihydrazinobenzoic acid hydrochloride in 2 mL of acetic acid, 0.54 mL of 3 methyl-2-butanone was added and the resulting mixture was heated at 130° C. for 2.5 hours. The volatile components were evaporated and the crude was purified by HPLC to yield 0.12 g of each derivative.

1.2 Preparation of C

[0235]

[0236]A mixture of 0.12 g of A and 0.56 mL of propane sultone and 0.5 mL of sulfolane was heated at 140° C. for 2.5 hours. The reaction mixture was cooled to room temperature and 5 mL of ethyl acetate was added and the supernatant was decanted. The resulting mixture was then heated in 5 mL of 1M HCl at 65° C. for 6 hours and the volatiles were evaporated. The crude material was used without further purification.

1.3 Preparation of D

[0237]

[0238]A mixture of 0.12 g of B and 0.56 mL of propane sultone and 0.5 mL of sulfolane was heated at 140° C. for 2.5 hours. The reaction mixture was cooled to room temperature and 5 mL of ethyl acetate w...

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PUM

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Abstract

The present invention provides heteroaryl functionalized cyanine dyes including a reactive functional moiety, or which are conjugated to a carrier molecule.

Description

FIELD OF INVENTION[0001]The present invention relates generally to reactive fluorescent compounds that are cyanine dyes, analogues of cyanine dyes and to conjugates of these dyes with carrier molecules. Exemplary compounds of the invention are fluorophores that are derivatized to allow their facile attachment to another moiety. The invention also relates to improved methods for sequencing and genotyping nucleic acids in a single molecule configuration. An exemplary method involves detection of single molecules of fluorescent labels released from a nucleic acid during synthesis of an oligonucleotide.BACKGROUND[0002]There is a continuous and expanding need for rapid, highly specific methods of detecting and quantifying chemical, biochemical and biological substances as analytes in research and diagnostic mixtures. Of particular value are methods for measuring small quantities of nucleic acids, peptides, saccharides, pharmaceuticals, metabolites, microorganisms and other materials of d...

Claims

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Application Information

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IPC IPC(8): G01N21/64
CPCG01N21/6486C07D495/04C09B57/00C07D487/04C09B23/06C09B23/08C09B23/0066C09B23/083
Inventor YUE, STEPHENSHEN, GENESUN, WEI-CHUAN
Owner PACIFIC BIOSCIENCES
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